Cuckold And Stockings And Heels Stories

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Public Humiliation

by bandanna1 on Sep 12, 2017
Fetish

My name is Julie, and I got into a catfight recently over a man. I had been to the same bar the night before and met a nice looking guy named Kevin, who was a lawyer. Talk about a good catch! We danced together a lot, had a good time, and arranged to meet the next night. When I arrived that night, Kevin was sitting at the same table as the night before, but...

Becoming Beth

by PantyPlay on Sep 16, 2017
Transsexuals & Crossdressers

When I entered hospice I was admitting that my money had failed to save my life. I'd visited doctors all over the world but I was still here, waiting for my time to come. Barely a year after contracting a disease doctors didn't even have a name for and my time was running out. But if nothing else, dying slowly gives you ample time for reflection. My forty y...

The Club Lounge

by themasseuse on Sep 16, 2017
Group Sex

I don’t get out much any more, but last month, Tonya and I wanted to get out, drink some and maybe catch some rock band. We decided to go see Spookyhorse and Dirty Little Secret at the Oasis Restaurant. We knew they wouldn’t come on till late so we decided to go early enough to get a few drinks, mingle and get ready for the show. That evening, I dressed i...

Desperate Measures

by Mr_Tamarind on Sep 16, 2017
Fetish

She read the letter again, of course it didn't say anything different from the last few times she had read it, damn the old bastard! She had been so close to getting it all signed and making her future safe when he went and died, now she was keenly aware that her decadent luxurious lifestyle was under threat and she wasn't sure what she should do about it....

Laura's Job Interview

by merlotus on Aug 31, 2017
Group Sex

All through the school year she had waited for the chance to apply for a summer job like this. She couldn't believe she might actually be hired to work in an art gallery. It was a chance not only to learn about art, but to dress up everyday as well. Such a welcome change from the conservative clothes she wore to college. She loved wearing skirts and heels, n...

The Adventures of Anna Clarke Ch. 03

by Prototype11 on Sep 14, 2017
Mature

Anna still standing outside Dave's house, now in an emotional battle trying to convince herself that she didn't do anything wrong. She continued to tell herself that she needed cock since her husband works away most of the year. What he does not know can't hurt him. But the guilt was so overwhelming knowing that she fucked a another man and his son. Knowing...

Caught Cheating Pt. 06

by Algonquin100 on Sep 14, 2017
Erotic Couplings

Andrew perched forward in his chair. He squinted as his eyes attempted to adjust to the small laptop screen. It seemed every time the IT department updated his computer, it got smaller. Andrew reviewed his email. Andy, Sam gave me the Telco update, thanks for all your help. I should be back at the end of the week- I'll use the weekend to update myself for...

Looking After All Their Needs Ch. 02

by Jack1107 on Jul 6, 2020
Mature

Jack had complimented his mum on her how she was dressing; she was now dressing much more casually but still smart; it made her look ten years younger. On Thursday night, mum suggested that after they had been to Dot's that they should go out for dinner somewhere. Jack suggested the Italian restaurant, which was a five-minute walk from their house, then they...

Walk a Mile in Her Shoes Ch. 04

by grgy56 on Sep 16, 2017
Transsexuals & Crossdressers

Standing next to Paul, both of us dressed up in our stereotypical, sexy maid outfits, I watched as Lori shut the front door on my girlfriend, Cheryl. Since Cheryl and Lori worked for the company, they made a little bet on whose boyfriend would finish the distance quickest in the "Walk a Mile in Her Shoes" march and who would collect more money in support of...

A Seasoned Slut

by laughingstock on Sep 14, 2017
Group Sex

I am perhaps the second most famous Eagles fan in all of Philadelphia—besides Birdman of course—I'm the Seasoned Slut! Allow me to explain. I bleed Philadelphia Eagles green. Season ticket holder—50 yard line I might add—and after a year sabbatical, the Birds were a cinch to qualify for the playoff tournament. This season it came down to the last game, but...